Phosphoric Acid → HCID 71727008, compound

HRID 1774241Notes

Reaction equation

HRID 1774241 reaction equation
[P:1](=[O:5])([OH:4])([OH:3])[OH:2].IN1C(=O)CCC1=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@H:21]([N:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][CH:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)[N:34]=3)=[CH:29][C:28]2=[O:46])[CH2:22][O:23][CH2:24]SC)=[CH:17][C:16]=1[F:47]>CN(C=O)C>[P:1]([OH:4])([OH:3])([O:2][CH2:24][O:23][CH2:22][C@H:21]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[C:16]([F:47])[CH:17]=1)[N:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([NH:39][CH:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)[N:34]=2)=[CH:29][C:28]1=[O:46])=[O:5]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 120273N-IodosuccinimideHCID 86696742HCID 86696742, compound

Product 1

HCID 71727008HCID 71727008, compoundYield 2.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphoric acid (0.40 g, 3.98 mmol), 4 Å molecular sieves (5 g) and N-iodosuccinimide (0.46 g, 1.99 mmol) were added to (S)-1-(1-(4-chloro-3-fluorophenyl)-2-((methylthio)methoxy)ethyl)-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.50 g, 1.00 mmol) in DMF (5 mL). The mixture was stirred at room temperature for 2 hours. The mixture was quenched with sodium thiosulfate. Sodium carbonate was added to bring pH to 10, and the solvent was removed. The resultant was purified by HPLC to afford (S)-(2-(4-chloro-3-fluorophenyl)-2-(2-oxo-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-1(2H)-yl)ethoxy)methyl dihydrogen phosphate (13 mg). M+1=555.1.

Workup

  1. customThe mixture was quenched with sodium thiosulfate
  2. additionSodium carbonate was added
  3. customthe solvent was removed
  4. customThe resultant was purified by HPLC

Sources & evidence

ORD record
ord-50961149ff384b87ac7d050acab38348
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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